Synthesis And Characterization Of3-(N-9-Adenine)Alanine And3-(N-1-Uracil)Alanine

Researches show that many nucleoside analogues are important industrial raw materials, prodrugs and drugs. Thus the development of nucleoside analogues has been a research hotspot. In this dissertation, the nucleoside analogues3-(N-9-adenine) alanine and3-(N-1-uracil) alanine were designed for synthesis and further study of their functions and application.Firstly, the3-halogenation of the N-(tert-butoxycarbonyl)-L-serine methyl ester was launched. By comparison of the yield and purity, chlorination is more efficient than iodination. Secondly, the chlorinated product methyl2-(tert-butoxycarbonyl)-3-chloropropanoate was used to react with adenine to give2-(tert-butoxycarbonyl)-3-(N-9-adenine) alanine methyl ester. After deamination reaction of2-(tert-butoxycarbonyl)-3-(N-9-adenine) alanine methyl ester, the product3-(N-9-adenine) alanine methyl ester was obtained. At the same time, the reaction conditions were optimized, and the influence of alkali species, temperature, reaction-time, the ratio of the reactants and solvent usage was discussed. Similarly,3-(N-1-uracil) alanine methyl ester was obtained. The target products can be obtained in the next step through the deprotection of3-(N-9-adenine) alanine methyl ester and3-(N-1-uracil) alanine methyl ester.It noted that the advantages of the method are mild reaction conditions, simplified operational procedure and high yield, providing a new way for the synthesis of nucleoside analogues. Structures of products3-(N-9-adenine) alanine methyl ester and3-(N-1-uracil) alanine methyl ester, which enrich the class of nucleoside compounds, were verified by MS,1H NMR,13C NMR and IR spectra. And their synthesis laid the foundation for further measure of the bioactivity.